CA2178479C - Chroman derivatives - Google Patents

Chroman derivatives Download PDF

Info

Publication number: CA2178479C
Authority: CA; Canada
Prior art keywords: compound; group; derivative according; chroman derivative; vitamin
Prior art date: 1993-12-07
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CA002178479A

Other languages

English (en)

French (fr)

Other versions

CA2178479A1 (en

Inventor

Koichi Shudo

Masashi Akaike

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Individual

Original Assignee

Individual

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1993-12-07

Filing date

1994-12-06

Publication date

2003-02-04

1994-12-06 Application filed by Individual filed Critical Individual

1995-06-15 Publication of CA2178479A1 publication Critical patent/CA2178479A1/en

2003-02-04 Application granted granted Critical

2003-02-04 Publication of CA2178479C publication Critical patent/CA2178479C/en

2014-12-06 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical class C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 title claims abstract description 42
125000000217 alkyl group Chemical group 0.000 claims abstract description 28
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 117
239000000203 mixture Substances 0.000 claims description 40
125000006239 protecting group Chemical group 0.000 claims description 8
239000000654 additive Substances 0.000 claims description 4
230000004913 activation Effects 0.000 claims description 3
208000011775 arteriosclerosis disease Diseases 0.000 claims description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
230000036512 infertility Effects 0.000 claims description 3
230000000302 ischemic effect Effects 0.000 claims description 3
230000004089 microcirculation Effects 0.000 claims description 3
230000000996 additive effect Effects 0.000 claims 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 15
125000003342 alkenyl group Chemical group 0.000 abstract description 12
125000003710 aryl alkyl group Chemical group 0.000 abstract description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 4
239000004480 active ingredient Substances 0.000 abstract description 3
229910052739 hydrogen Inorganic materials 0.000 abstract description 3
239000013543 active substance Substances 0.000 abstract description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 abstract description 2
239000001257 hydrogen Substances 0.000 abstract 1
150000001875 compounds Chemical class 0.000 description 98
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 75
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 60
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 38
238000005160 1H NMR spectroscopy Methods 0.000 description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
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VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 20
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239000003814 drug Substances 0.000 description 19
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229930003427 Vitamin E Natural products 0.000 description 18
WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 18
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WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
101150041968 CDC13 gene Proteins 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
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DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
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235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
230000000934 organogenetic effect Effects 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000002985 plastic film Substances 0.000 description 1
229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
229920001083 polybutene Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000012264 purified product Substances 0.000 description 1
239000008213 purified water Substances 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000002639 sodium chloride Nutrition 0.000 description 1
NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
229940032147 starch Drugs 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
238000012353 t test Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
239000010936 titanium Substances 0.000 description 1
229930003802 tocotrienol Natural products 0.000 description 1
239000011731 tocotrienol Substances 0.000 description 1
235000019148 tocotrienols Nutrition 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
210000004291 uterus Anatomy 0.000 description 1
229940099259 vaseline Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
- C07D311/72—3,4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Reproductive Health (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Endocrinology (AREA)
Urology & Nephrology (AREA)
Gynecology & Obstetrics (AREA)
Toxicology (AREA)
Diabetes (AREA)
Hematology (AREA)
Obesity (AREA)
Biochemistry (AREA)
Pregnancy & Childbirth (AREA)
Nutrition Science (AREA)
Vascular Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Pyrane Compounds (AREA)
Saccharide Compounds (AREA)
Anti-Oxidant Or Stabilizer Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA002178479A 1993-12-07 1994-12-06 Chroman derivatives Expired - Fee Related CA2178479C (en)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
JP340012/1993		1993-12-07
JP34001293		1993-12-07
JP17523194A JP3839071B2 (ja)	1993-12-07	1994-07-27	クロマン誘導体
JP175231/1994		1994-07-27
PCT/JP1994/002046 WO1995015957A1 (en)	1993-12-07	1994-12-06	Chroman derivative

Publications (2)

Publication Number	Publication Date
CA2178479A1 CA2178479A1 (en)	1995-06-15
CA2178479C true CA2178479C (en)	2003-02-04

Family

ID=26496563

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002178479A Expired - Fee Related CA2178479C (en)	1993-12-07	1994-12-06	Chroman derivatives

Country Status (9)

Country	Link
US (1)	US5719180A (de)
EP (1)	EP0732329B1 (de)
JP (1)	JP3839071B2 (de)
KR (1)	KR100487060B1 (de)
AT (1)	ATE215943T1 (de)
AU (1)	AU713777B2 (de)
CA (1)	CA2178479C (de)
DE (1)	DE69430383T2 (de)
WO (1)	WO1995015957A1 (de)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5798356A (en) *	1995-08-07	1998-08-25	Alcon Laboratories, Inc.	Angiostatic compounds
ES2282326T3 (es) *	2000-10-24	2007-10-16	Cis Bio International	Estabilizacion de composiciones radio-farmaceuticas usando tioeteres hidrofilicos o 6-hidroxicromanos hidrofilicos.
WO2004026842A1 (ja) *	2002-09-20	2004-04-01	Sumitomo Pharmaceuticals Co., Ltd.	新規ウラシル誘導体及びその医薬用途
ITTO20030140U1 (it) *	2003-09-16	2005-03-17	Interfila Srl	Matita cosmetica
WO2005033093A1 (en)	2003-09-19	2005-04-14	Galileo Pharmaceuticals, Inc.	7,8-bicycloalkyl-chroman derivatives
WO2010024903A1 (en) *	2008-08-29	2010-03-04	Yangbo Feng	BENZO[d]OXAZOLES AND BENZO[d]THIAZOLES AS KINASE INHIBITORS
KR20130055595A (ko)	2010-04-15	2013-05-28	크로모셀 코포레이션	쓴맛을 감소시키거나 제거하기 위한 화합물, 조성물 및 방법
HK1201177A1 (en)	2011-10-20	2015-08-28	Chromocell Corporation	Compounds, compositions, and methods for reducing or eliminating bitter taste
WO2019185894A1 (en) *	2018-03-29	2019-10-03	Dsm Ip Assets B.V.	Novel use of substituted chroman-6-ols
WO2019185904A1 (en) *	2018-03-29	2019-10-03	Dsm Ip Assets B.V.	Chroman-6-ols with an extended lipophilic side chain in position 2, their manufacture and use

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH506516A (de) *	1968-02-27	1971-04-30	Hoffmann La Roche	Verfahren zur Herstellung von Chromanolen
CH547278A (de) *	1971-01-11	1974-03-29	Hoffmann La Roche	Verfahren zur herstellung von chromanderivaten.
CH619701A5 (de) *	1975-08-07	1980-10-15	Bayer Ag
JPS62292777A (ja) *	1986-06-12	1987-12-19	Daikin Ind Ltd	含フツ素クロマン類
CA2019884A1 (en) *	1989-07-07	1991-01-07	Yoshiharu Fukui	Food container
JP2813891B2 (ja) *	1989-07-07	1998-10-22	住友化学工業株式会社	食品容器
US5149834A (en) *	1990-03-07	1992-09-22	Fujirebio Inc.	4-hydroxytetrahydropyran-2-one derivatives
FR2679904A1 (fr) *	1991-08-01	1993-02-05	Lvmh Rech	Utilisation d'un phosphate de tocopherol, ou de l'un de ses derives, pour la preparation de compositions cosmetiques, ou pharmaceutiques et compositions ainsi obtenues.
SG48108A1 (en) *	1991-11-22	1998-04-17	Lipogenenics Inc	Tocotrienols and tocotrienol-like compounds and methods for their use

1994
- 1994-07-27 JP JP17523194A patent/JP3839071B2/ja not_active Expired - Fee Related
- 1994-12-06 AT AT95902305T patent/ATE215943T1/de not_active IP Right Cessation
- 1994-12-06 US US08/656,254 patent/US5719180A/en not_active Expired - Lifetime
- 1994-12-06 EP EP95902305A patent/EP0732329B1/de not_active Expired - Lifetime
- 1994-12-06 DE DE69430383T patent/DE69430383T2/de not_active Expired - Lifetime
- 1994-12-06 WO PCT/JP1994/002046 patent/WO1995015957A1/ja not_active Ceased
- 1994-12-06 CA CA002178479A patent/CA2178479C/en not_active Expired - Fee Related
- 1994-12-06 AU AU11211/95A patent/AU713777B2/en not_active Ceased
- 1994-12-06 KR KR1019960703007A patent/KR100487060B1/ko not_active Expired - Fee Related

Also Published As

Publication number	Publication date
JP3839071B2 (ja)	2006-11-01
HK1017575A1 (en)	1999-11-19
EP0732329B1 (de)	2002-04-10
DE69430383D1 (de)	2002-05-16
KR100487060B1 (ko)	2005-08-23
WO1995015957A1 (en)	1995-06-15
EP0732329A4 (de)	1996-07-24
CA2178479A1 (en)	1995-06-15
KR960706486A (ko)	1996-12-09
AU1121195A (en)	1995-06-27
DE69430383T2 (de)	2002-11-07
US5719180A (en)	1998-02-17
JPH07215959A (ja)	1995-08-15
AU713777B2 (en)	1999-12-09
ATE215943T1 (de)	2002-04-15
EP0732329A1 (de)	1996-09-18

Legal Events

Date	Code	Title	Description
1998-12-14	EEER	Examination request
2011-12-06	MKLA	Lapsed

Publication	Publication Date	Title
NO871961L (no)	1987-11-16	Tetrahydronaftalinderivater.
CA2178479C (en)	2003-02-04	Chroman derivatives
JPH04330088A (ja)	1992-11-18	グリチルレチン酸誘導体
WO2001028329A1 (en)	2001-04-26	Peripheral cannabinoid receptor (cb2) selective ligands
CN115477681A (zh)	2022-12-16	一种五环三萜皂苷衍生物及制备方法与应用
CN101863786B (zh)	2013-05-01	水溶性紫草素萘茜母核氧烷基化衍生物及其制备和应用方法
US20080234258A1 (en)	2008-09-25	Dihydroxyanthraquinones and Their Use
KR100406736B1 (ko)	2003-11-21	나프토퀴논계 화합물을 포함하는 항암제
US5698585A (en)	1997-12-16	Pharmaceutical preparation for prevention and/or treatment for cataract
JP2782117B2 (ja)	1998-07-30	リン脂質誘導体
JP2761023B2 (ja)	1998-06-04	新規安息香酸誘導体及びその製造方法
RS51576B (sr)	2011-08-31	Bifenil i naftil-fenil derivati hidroksamske kiseline
JPH08231396A (ja)	1996-09-10	抗ヘリコバクター・ピロリ薬
KR100355131B1 (ko)	2003-02-05	7-글리코실옥시벤조피란유도체및이를활성성분으로서함유하는항알레르기성약제학적조성물
JP3225518B2 (ja)	2001-11-05	ベンゾピラン誘導体並びにそれを有効成分とする抗アレルギー剤
US4975454A (en)	1990-12-04	Triene compounds having a chromene structure
JP3150740B2 (ja)	2001-03-26	ジヒドロベンゾフラン誘導体
JP2012097003A (ja)	2012-05-24	ビキシン誘導体及び細胞保護剤
JPH08217672A (ja)	1996-08-27	キサントン誘導体を含有する抗ヘリコバクター・ピロリ薬
US6071898A (en)	2000-06-06	Asiatic acid derivatives having modified A-ring
HK1017575B (en)	2002-09-13	Chroman derivative
JPH07258074A (ja)	1995-10-09	新規な血行促進のために使用する医薬
JPH09165394A (ja)	1997-06-24	新規リン酸ジエステル
JPH05221915A (ja)	1993-08-31	１，４−ベンゾキノン誘導体
KR101634758B1 (ko)	2016-06-30	에스트로겐 수용체 리간드로서의 2-하이드록시-7-메틸 옥타하이드로페난트렌 유도체 또는 이의 약학적으로 허용가능한 염을 유효성분으로 함유하는 약학 조성물